Amino derivatives of 4-phenyl 4-oxobuten-2-oic acid, pharmaceutical compositions containing them, and methods for preparing and therapeutically using them

Abstract

Compounds of the formula I: <IMAGE> in which R represents a hydrogen atom or an alkyl radical containing from 1 to 8 carbon atoms and R1 and R2, which may be identical or different independently represent a hydrogen atom, an alkyl radical containing from 1 to 4 carbon atoms, a -CONH2 radical, a -CO2alk1 radical in which alk1 represents an alkyl radical containing from 2 to 8 carbon atoms, or an-SO2alk2 radical in which alk2 represents an alkyl radical containing from 1 to 8 carbon atoms, or R1 and R2 together with the nitrogen atom form a heterocycle provided that R1 and R2 are not both hydrogen, as well as the alkali metal, alkaline earth metal, ammonium or amine salts of compounds of formula I in which R represents a hydrogen atom. These compounds are useful in treating hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias and gastric or gastroduodenal ailments accompanied by gastric hyperacidity. The invention includes pharmaceutical compositions comprising compounds of formula (I) as well as methods of making the compounds.

What is claimed is: 
     
       1. A compound of formula I: ##STR5## in which R represents a hydrogen atom or an alkyl radical containing from 1 to 8 carbon atoms and R 1  and R 2  independently represent a hydrogen atom, an alkyl radical containing from 1 to 4 carbon atoms, a --CONH 2  radical, --CO 2  alk 1  radical in which alk 1  represents an alkyl radical containing from 2 to 8 carbon atoms, or an --SO 2  alk 2  radical in which alk 2  represents an alkyl radical containing from 1 to 8 carbon atoms or R 1  and R 2  together with the nitrogen atom form a heterocycle selected from the group consisting of morpholine and N-methyl piperazine, provided that R 1  and R 2  are not both hydrogen, as well as the pharmaceutically acceptable alkali metal, alkaline earth metal, ammonium or amine salts of the said compounds of formula I when R represents a hydrogen atom. 
     
     
       2. A compound of formula I as defined in claim 1 in which R represents a hydrogen atom, or an alkali metal, alkaline earth metal, ammonium or amine salt thereof. 
     
     
       3. A compound of formula I as defined in claim 1 in which R 1  represents a hydrogen atom. 
     
     
       4. A compound of formula I as defined in claim 2 in which R 1  represents a hydrogen atom. 
     
     
       5. A compound of formula I as defined in claim 1 in which R 2  is selected from the group consisting of a --CO 2  C 2  H 5  radical, a --CONH 2  radical and an --SO 2  CH 3  radical. 
     
     
       6. A compound of formula I s defined in claim 2 in which R 2  is selected from the group consisting of a --CO 2  C 2  H 5  radical, a --CONH 2  radical and an --SO 2  CH 3  radical. 
     
     
       7. A compound of formula I as defined in claim 3 in which R 2  is selected from a group consisting of a --CO 2  C 2  H 5  radical, a --CONH 2  radical and an --SO 2  CH 3  radical. 
     
     
       8. A compound of formula I as defined in claim 4 in which R 2  is selected from the group consisting of a --CO 2  C 2  H 5  radical, a --CONH 2  radical and an --SO 2  CH 3  radical. 
     
     
       9. A compound of formula I as defined in claim 1 in which R 1  and R 2  each represent a methyl radical. 
     
     
       10. A compound of formula I as defined in claim 2 in which R 1  and R 2  each represent a methyl radical. 
     
     
       11. (E) 4-(4-carbethoxyaminophenyl)-4-oxobuten-2-oic acid as well as a pharmaceutically acceptable alkali metal, alkaline earth metal, ammonium or amine salt thereof. 
     
     
       12. A pharmaceutical composition for treating hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising a therapeutically effective amount of a compound of formula (I) as defined in claim 1 and a pharmaceutically acceptable excipient. 
     
     
       13. A pharmaceutical composition for treating hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising a therapeutically effective amount of a compound of formula (I) as defined in claim 2 and a pharmaceutically acceptable excipient. 
     
     
       14. A pharmaceutical composition for treating hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising a therapeutically effective amount of a compound of formula (I) as defined in claim 3 and a pharmaceutically acceptable excipient. 
     
     
       15. A pharmaceutical composition for treating hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising a therapeutically effective amount of a compound of formula (I) as defined in claim 5 and a pharmaceutically acceptable excipient. 
     
     
       16. A pharmaceutical composition for treating hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising a therapeutically effective amount of a compound of formula (I) as defined in claim 8 and a pharmaceutically acceptable excipient. 
     
     
       17. A pharmaceutical composition for treating hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising a therapeutically effective amount of a compound as defined in claim 10 and a pharmaceutically acceptable excipient. 
     
     
       18. A method of treating a patient suffering from hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising administering to said patient a therapeutically effective amount of a compound of formula (I) as defined in claim 1. 
     
     
       19. A method of treating a patient suffering from hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising administering to said patient a therapeutically effective amount of a compound of formula (I) as defined in claim 2. 
     
     
       20. A method of treating a patient suffering from hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising administering to said patient a therapeutically effective amount of a compound of formula (I) as defined in claim 3. 
     
     
       21. A method of treating a patient suffering from hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising administering to said patient a therapeutically effective amount of a compound of formula (I) as defined in claim 5. 
     
     
       22. A method of treating a patient suffering from hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising administering to said patient a therapeutically effective amount of a compound of formula (I) as defined in claim 8. 
     
     
       23. A method of treating a patient suffering from hyperchlorhydria, gastric or gastroduodenal ulcers, gastritis, hiatal hernias, or gastric or gastroduodenal ailments accompanied by gastric hyperacidity, comprising administering to said patient a therapeutically effective amount of a compound as defined in claim 10. 
     
     
       24. A method as claimed in claim 18, wherein said compound is administered by digestive route. 
     
     
       25. A method as claimed in claim 18, wherein said compound is administered parenterally. 
     
     
       26. A compound according to claim 1 which is (E) 4-(4-N,N-dimethylamino phenyl) 4-oxobuten-2-oic acid as well as the pharmaceutically acceptable alkali metal, alkaline earth metal, ammonium or amine salts thereof.